Every two years, more than 100 owners and crews of the world’s most sought-after sailboat brand come together for the Rolex Swan Cup, a five-day race series held at the Yacht Club Costa Smeralda. The regatta takes place on the northern coast of Sardinia, with its famed Mistral winds, and attracts owners from three continents to compete for two sweet prizes—a Rolex watch and, equally as important, winner’s bragging rights.